Compound for organic electric element, organic electric element comprising the same and electronic device thereof

ABSTRACT

The present invention provides the compound represented by Formula 1, and an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises the compound represented by Formula 1. The driving voltage of an organic electronic device can be lowered, and the luminous efficiency, color purity and life time of an organic electronic device can be improved by comprising the compound represented by Formula 1 in the organic material layer.

BACKGROUND Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements comprising the same, and electronicdevices thereof.

Background Art

Polycyclic ring compound containing heteroatoms has very differentcharacteristics depending on the material structure, and thus it isbeing applied as material of various layers of OLED.

In particular, the heterocyclic compound is characterized in that theband gap (HOMO, LUMO), electrical characteristics, chemical properties,and physical properties are different depending on the number of ringsand fused positions, the kind and arrangement of heteroatoms. Therefore,it has been developed and applied to various OLED layers (HTL orphosphorescent host: U.S. Pat. No. 8,334,058, KR 1108398; applied asETL: KR 0813385, KR 0765078).

Recently, OLED materials have been actively developed for the kind,number; and positions of heteroatoms in the 5-membered ring compound (KR1418146, KR 0938796, KR 2011-0043439, KR 20112-0140557, KR 2013-0071547,JP 2010-230312, etc.).

Object, Technical Solution and Effects of the Invention

An object of the present invention is to provide a compound allowing adriving voltage to lower, luminous efficiency to improve and lifetime tooptimize by using the characteristics of polycyclic ring compound, anorganic electric element employing the same, and an electric devicethereof.

In accordance with an aspect of the present invention, the presentinvention provides the compound represented by the following Formula.

In another aspect of the present invention, organic electric elementscomprising the compound represented by the formula 1 above andelectronic devices including the organic electric element are provided.

By using the compound according to embodiments of the present invention,driving voltage of the element can be lowered, and luminous efficiency,color purity and life span of the element can be remarkably improved.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention: 100 is organicelectric element, 110 is substrate, 120 is first electrode, 130 is holeinjection layer, 140 is hole transport layer, 141 is buffer layer, 150is light emitting layer, 151 is emission-auxiliary layer, 160 iselectron transport layer, 170 is electron injection layer, and 180 issecond electrode.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used for defining an essence, orderor sequence of a corresponding component but used merely to distinguishthe corresponding component from other component(s). It should be notedthat if it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

In addition, it will be understood that when an element such as a layer,film, region or substrate is referred to as being “on” or “over” anotherelement, it can be directly on the other element or intervening elementsmay also be present. In contrast, when an element is referred to asbeing “directly on” another element, there are no intervening elementspresent.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means aliphaticfunctional radicals including a linear alkyl group, a branched chainalkyl group, a cycloalkyl group (alicyclic), or an alkyl groupsubstituted with a cycloalkyl.

Unless otherwise stated, the term “halo alkyl” or “halogen alkyl” asused herein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxyl group”, “alkoxy group” or “alkyloxy group” as usedherein means an oxygen radical attached to an alkyl group, but notlimited to, and has 1 to 60 carbon atoms.

The term “aryloxyl group” or “aryloxy group” as used herein means anoxygen radical attached to an aryl group, but not limited to, and has 6to 60 carbon atoms.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means, univalent or bivalent functional groupwhich R, R′ and R″ are all hydrogen in the structural formula below,“substituted fluorenyl group” or “substituted fluorenylene group” means,functional group which at least any one of R, R′ and R″ is a functionalgroup other than hydrogen, and fluorenyl group” or “fluorenylene group”comprises spiro compound which is formed by linking R and R′ togetherwith the carbon bonded to them.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. The arylgroup or arylene group include a monocyclic rings, ring assemblies,fused polycyclic system or spiro compounds.

Unless otherwise stated, the term “heterocyclic group” as used hereinmeans, but not limited to, a non-aromatic ring as well as an aromaticring like “heteroaryl group” or “heteroarylene group”. The heterocyclicgroup as used herein means, but not limited to, a ring containing one ormore heteroatoms, and having 2 to 60 carbon atoms. Unless otherwisestated, the term “heteroatom” as used herein represents N, O, S, P orSi. The heterocyclic group means a monocyclic, ring assemblies, fusedpolycyclic system or spiro compound containing one or more heteroatoms.

Also, the term “heterocyclic group” may include SO₂ instead of carbonconsisting of cycle. For example, “heterocyclic group” includes thefollowing compound.

Unless otherwise stated, the term “ring” as used herein means, amonocyclic and polycyclic, an aliphatic ring and heterocyclic groupcontaining at least one heteroatom, and an aromatic ring and anon-aromatic ring.

Unless otherwise stated, the term “polycyclic” as used herein means,ring assemblies like biphenyl and terphenyl, fused polycyclic system andspiro compound, an aromatic ring and a non-aromatic ring, and analiphatic ring and heterocyclic group containing at least oneheteroatom.

Unless otherwise stated, the term “ring assemblies” as used hereinmeans, two or more cyclic systems (single rings or fused systems) whichare directly joined to each other by double or single bonds are namedring assemblies when the number of such direct ring junctions is oneless than the number of cyclic systems involved. The ring assembliesalso mean, same or different ring systems are directly joined to eachother by double or single bonds.

Unless otherwise stated, the term “fused polycyclic system” as usedherein means, fused ring type which has at least two atoms as the commonmembers, fused two or more aliphatic ring systems and a fused heteroring system containing at least one heteroatom. Fused polycyclic systemis an aromatic ring, a hetero aromatic ring, an aliphatic ring, or thecombination of these.

Unless otherwise stated, the term “spiro compound” as used herein has, aspiro union which means union having one atom as the only common memberof two rings. The common atom is designated as ‘spiro atom’. Thecompounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’depending on the number of spiro atoms in one compound.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substitutes with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthio group, a C₆-C₂₀ arylthio group, a C₂-C₂₀ alkenyl group,a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₆₀ aryl group,a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ arylalkenylgroup, a silane group, a boron group, a germanium group, and a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P.

In the present description, a ‘group name’ corresponding to an arylgroup, an arylene group, a heterocyclic group, and the like exemplifiedfor each symbol and its substituent may be written in the name offunctional group reflecting the valence, and may also be described underthe name of a parent compound. For example, in the case of phenanthrenewhich is a kind of aryl group, it may be described by distinguishingvalence such as ‘phenanthryl (group)’ when it is ‘monovalent group’, andas ‘phenanthrylene (group)’ when it is ‘divalent group’, and it may alsobe described as a parent compound name, ‘phenanthrene’, regardless ofits valence. Similarly, in the case of pyrimidine, it may be describedas ‘pyrimidine’ regardless of its valence, and it may also be describedas the name of corresponding functional group such as pyrimidinyl(group) when it is ‘monovalent group’, and as ‘pyrimidylene (group)’when it is ‘divalent group’.

Otherwise specified, the formulas used in the present invention are asdefined in the index definition of the substituent of the followingformula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R¹s may be the same and different, and are linked tothe benzene ring as follows. when a is an integer of 4 to 6, thesubstituents R¹s may be the same and different, and are linked to thebenzene ring in a similar manner to that when a is an integer of 2 or 3,hydrogen atoms linked to carbon constituents of the benzene ring beingnot represented as usual.

The FIGURE illustrates an organic electric element according to anembodiment of the present invention.

Referring to the FIGURE, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer between the first electrode 110 and the second electrode180, which contains the inventive compound. Here, the first electrode120 may be an anode (positive electrode), and the second electrode 180may be a cathode (negative electrode). In the case of an invertedorganic electric element, the first electrode may be a cathode, and thesecond electrode may be an anode.

The organic material layer may include a hole injection layer 130, ahole transport layer 140, a light emitting layer 150, an electrontransport layer 160, and an electron injection layer 170 formed insequence on the first electrode 120. Here, at least one layer of theorganic material layer may be omitted, the organic material layer mayfurther include a hole blocking layer, an electron blocking layer, anemission-auxiliary layer 151, an electron transport auxiliary layer, abuffer layer 141, etc., and the electron transport layer 160 or the likemay serve as the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer or one capping layer formed on at least one of thesides the first and second electrodes, which is a side opposite to theorganic material layer.

The inventive compound employed in the organic material layer may beused as a material of a hole injection layer 130, a hole transport layer140, an electron transport layer 160, an electron transport auxiliarylayer, as a host or a dopant material of a light emitting layer 150, oras a material of a capping layer. For example, the inventive compoundmay be used as material of the light emitting layer 150, the holetransport layer 140, and/or the emission-auxiliary layer 151,preferably, as the hole transport layer 140, and/or theemission-auxiliary layer 151.

On the other hand, even if the core is the same core, the band gap, theelectrical characteristics, the interface characteristics, and the likemay be different depending on which substituent is bonded at whichposition. Therefore, it is necessary to study the selection of the coreand the combination of the sub-substituent. Specially, long life spanand high efficiency can be simultaneously achieved when the optimalcombination of energy levels and T1 values, inherent material properties(mobility, interfacial properties, etc.), and the like among therespective layers of an organic material layer is achieved.

According to the present invention, energy levels and T₁ values betweenorganic material layers, inherent material properties (mobility,interfacial properties, etc.), and the like can be optimized by forminga hole transport layer 140 and/or a light emitting layer 150 whichcomprise the compound represented by the Formula 1, and thus it ispossible to simultaneously improve the life span and efficiency of theorganic electronic element.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 120, forming the organic material layer including the holeinjection layer 130, the hole transport layer 140, the light emittinglayer 150, the electron transport layer 160, and the electron injectionlayer 170 thereon, and then depositing a material, which can be used asthe cathode 180, thereon. Also, an emission-auxiliary layer 151 may beformed between a hole transport layer 140 and a light emitting layer150, and an electron transport auxiliary layer may be formed between alight emitting layer 150 and an electron transport layer 160.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transfer,instead of deposition. Since the organic material layer according to thepresent invention may be formed in various ways, the scope of protectionof the present invention is not limited by a method of forming theorganic material layer.

The organic electric element according to an embodiment of the presentinvention may be of a top emission type, a bottom emission type, or adual emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization, an excellent processability, and being producedby using conventional color filter technologies for LCDs. Variousstructures for WOLED which mainly used as back light units have beensuggested and patented. WOLED may employ various arrangement methods,representatively, a parallel side-by-side arrangement method of R (Red),G (Green), B (Blue) light-emitting units, a vertical stack arrangementmethod of RGB light-emitting units, and a CCM (color conversionmaterial) method in which electroluminescence from a blue (B) organiclight emitting layer, and the present invention may be applied to suchWOLED.

Also, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode, anorganic solar cell, an organic photo conductor, an organic transistor,and an element for monochromatic or white illumination.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, an organic electric element according to an aspect of thepresent invention will be described.

The compound according to an aspect of the present invention isrepresented by the following Formula 1.

In Formula 1 above, each of symbols may be defined as follows.

X and Y are each independently O, S, C(R¹³)(R¹⁴) or Si(R¹³)(R¹⁴). m andn are each an integer of 0 or 1, and m+n is an integer of 1 or more,when m and n are each 0, each bridge Y and X mean single bonds. At thistime, in C(R¹³)(R¹⁴) or Si(R¹³)(R¹⁴), R¹³ and R¹⁴ are each independentlyselected from the group consisting of hydrogen, deuterium, a C₁-C₅₀alkyl group, a C₂-C₃₀ alkenyl group, a C₂-C₃₀ alkynyl group, a C₁-C₃₀alkoxyl group, a C₆-C₃₀ aryloxyl group, a C₁-C₃₀ Silyl group, a C₆-C₆₀aryl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afluorenyl group, a fused ring group of a C₆-C₆₀ aromatic ring and aC₃-C₆₀ aliphatic ring, and a group consisting of -L′-N(R^(a))(R^(b)).R¹³ and R¹⁴ may be linked to each other to form a spiro-compoundtogether with C or Si to which they are bonded.

When R¹³ and R¹⁴ are an alkyl group, preferably, they may be a C₁-C₁₀alkyl group, for example, methyl group.

When R¹³ and R¹⁴ are an aryl group, preferably, they may be a C₆-C₁₈aryl group, for example, phenyl and the like.

R¹ to R¹² are each independently selected from the group consisting ofhydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenyl group, aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si and P, a fused ring group of aC₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring, a C₁-C₅₀ alkyl group,a C₂-C₂₀ alkenyl group, a C₁-C₅₀ alkynyl group, a C₁-C₃₀ alkoxyl group,a C₆-C₃₀ aryloxyl group and -L′-N(R^(a))(R^(b)).

In addition to, neighboring groups of R¹ to R¹² may be linked to eachother to form a ring. For example, neighboring R¹ and R², neighboring R²and R³, neighboring R³ and R⁴, neighboring R⁶ and R⁷, neighboring R⁸ andR⁹, neighboring R⁹ and R¹⁰, or neighboring R¹⁰ and R¹¹ may be linked toeach other to form a ring.

The ring formed by linking between neighboring groups of R¹ to R¹² maybe a C₆-C₆₀ aromatic ring, a fluorene, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, or a fused ring group of a C₆-C₆₀ aromatic ring anda C₃-C₆₀ aliphatic ring. For example, the ring formed by linking betweenneighboring groups of R¹ to R¹² may be benzene, and the like, and thus,naphthalene, phenanthrene and the like may be formed together withbenzene ring to which they are bonded.

When R¹ to R¹² are an aryl group, they may be preferably a C₆-C₃₀ arylgroup, more preferably a C₆-C₁₈ aryl group, for example, phenyl,naphthyl, biphenyl, terphenyl and the like. When R¹ to R¹² are aheterocyclic group, they may be preferably a C₂-C₃₀ heterocyclic group,more preferably a C₂-C₂₅ heterocyclic group, for example, pyridyl,carbazol, dibenzothienocarbazole, dibenzofurocarbazole,9,9-dimethyl-9H-fluorenocarbazole and the like. When R¹ to R¹² are afluorenyl group, they may be 9,9-dimethyl-9H-fluorene and the like.

L¹ may be selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a fluorenylene group; a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P; a fused ring of a C₆-C₆₀ aromatic ring and a C₃-C₆₀aliphatic ring.

When L¹ is an arylene group, L¹ may be a C₆-C₃₀ arylene group,preferably a C₆-C₁₈ arylene group, for example, phenylene; when L¹ is aheterocyclic group, L¹ may be preferably a C₂-C₃₀ heterocyclic group,more preferably a C₂-C₂₅ heterocyclic group, for example, pyrimidine,triazine, quinazoline, carbazole, dibenzothiophene, dibenzofuran,benzoquinazoline, dibenzoquinazoline, benzothienopyrimidine,benzofuropyrimidine, naphthothienopyrimindine, naphthofuropyrinmidine,phenanthrothienopyrimidine, phenanthrofurfuropyrimidine,dibenzothienocarbazole, dibenzofurocarbazole,9,9-dimethyl-9H-fluorenocarbazole, and the like. When L¹ is afluorenylene group, L¹ may be 9,9-dimethyl-9H-fluorene.

Ar¹ is selected from the group consisting of a C₆-C₆₀ aryl group, afluorenyl group, a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si, and P,-L′-N(R^(a))(R^(b)).

When Ar¹ is an aryl group, Ar¹ may be preferably a C₆-C₃₀ aryl group,more preferably a C₆-C₁₈ aryl group, for example, phenyl, biphenyl,terphenyl, naphthalene, pyrene and the like. When Ar¹ is a heterocyclicgroup, Ar¹ may be preferably a C₂-C₃₀ heterocyclic group, morepreferably a C₂-C₂₆ heterocyclic group, for example, pyridine,pyrimidine, quinazoline, carbazole, thianthrene, dibenzothiopiiene,dibenzofuran, benzoquinazoline, dibenzoquinazoline,benzothienopyrimidine, benzofuropyrimidine, naphthothienopyrimidine,naphthofuropyrimidine, phenanthrothienopyrimidine,phenanthrofuropyrimidine, dibenzothihenocarbazole, dibenzofurocarbazole,9,9-dimethyl-9H-fluorenocarbazole,dibydrobenzo[b]benzosilobenzocarbazole, diphenyl-dihydrobenzo[b]benzosilobenzocarbazole and the like. When Ar¹ is afluorenylene group, Ar¹ may be 9,9-dimethyl-9H-fluorene.

In -L′-N(R^(a))(R^(b)) above, L′ may be selected from the groupconsisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylenegroup; a C₂-C₆₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P; a fused ringof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, and L′ may befurther substituted with substituent. For example, L′ may be furthersubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group, a siloxane group, aboron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkyl group, aC₇-C₂₀ arylalkyl group, a C₈-C₂₀ arylalkenyl group and —N(R^(a))(R^(b)).

When L′ is an arylene group, L′ may be a C₆-C₃₀ arylene group,preferably a C₆-C₁₈ arylene group, for example, phenylene, biphenyl,terphenyl, and the like; when L′ is a heterocyclic group, L′ may bepreferably a C₆-C₃₀ heterocyclic group, more preferably a C₆-C₁₂heterocyclic group, for example, dibenzothiophene; when L′ is afluorenylene group, L′ may be 9,9-dimethyl-9H-fluorene.

In -L′-N(R^(a))(R^(b)) and —N(R^(a))(R^(b)) above, R^(a) and R^(b) maybe each independently selected from the group consisting of a C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P; a fused ring of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring.

When R^(a) and R^(b) are a C₆-C₆₀ aryl group, R^(a) and R^(b) may bepreferably a C₆-C₃₀ aryl group, more preferably a C₆-C₁₄ aryl group, forexample, phenyl, biphenyl, naphthyl, phenanthrene and the like. WhenR^(a) and R^(b) are a heterocyclic group, R^(a) and R^(b) may bepreferably C₂-C₃₀ heterocyclic group, more preferably C₂-C₂₆heterocyclic group, for example, dibenzothiophene, dibenzofuran,carbazole, benzocarbazole and the like. When R^(a) and R^(b) are afluorenyl group, R^(a) and R^(b) may be 9,9-dimethyl-9H-fluorene,9,9′-spirobifluorene and the like.

Preferably, in -L′-N(R^(a))(R^(b)), L′ may be any one selected from thegroup consisting of the following Formulas.

In group of the above formulas, R²¹ to R²³ are each independentlyselected from the group consisting of hydrogen, deuterium, halogen, asilane group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxylgroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₆-C₂₀ arylgroup, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenylgroup, a C₂-C₂₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P, a C₃-C₂₀cycloalkyl group, a C₇-C₂₀ arylalkyl group, a C₈-C₂₀ arylalkenyl group,and —N(R)(R). In N(R)(R), R and R^(b) are the same as defined above.

b1 is an integer of 0 to 4, b2 is an integer of 0 to 6, b3 is an integerof 0 to 5, and b4 is an integer of 0 to 8. When b1 to b4 are each aninteger of 2 or more, neighboring groups of R²¹ to R²³ may be linked toeach other to form a ring. Here, the formed ring may be a C₆-C₆₀aromatic ring, a fluorene, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, or a fused ring of a C₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphaticring.

In group of the above formulas group, A is an N(Ar²), O, S, C(R¹³)(R¹⁴)or Si(R¹³)(R¹⁴), wherein Ar² is the same as Ar¹ defined in formula 1 andR³ and R⁴ are the same as defined in formula 1.

In formula 1, when each symbol is an aryl group, a fluorenyl group, aheterocyclic group, a fused ring group, an arylene group, an alkylgroup, an alkenyl group, an alkynyl group, an alkynyl group, an alkoxylgroup, an aryloxy group or fluorenylene group, they may be eachoptionally further substituted with deuterium, halogen, a silane group,a siloxane group, a boron group, a germanium group, a cyano group, anitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group, C₁-C₂₀alkyl group, C₂-C₂₀ alkenyl group, C₂-C₂₀ alkynyl group, a C₆-C₂₀ arylgroup, a C₆-C₂₀ aryl group substituted with deuterium, a C₃-C₂₀cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenylgroup.

When m is 0 and n is 1 in the above formula 1, formula 1 may berepresented by the following formula 2, and when m is 1 and n is 0 inthe above formula 1, formula 1 may be represented by the followingformula 3.

In formulas 2 and 3 above, each of R¹ to R¹², Ar¹, L¹, X, Y and the likeis the same as defined in formula 1 above.

Preferably, in formulas 1 to 3 above, Ar¹ may be a C₆-C₂₀ aryl grouprepresented by

or a C₂-C₆₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P, for example,any one of the following formulas Z-10 to Z-22.

In formulas Z-1 to Z-22 above, Ar³ is the same as Ar¹ defined in formula1, and W¹ and W² are each independently a single bond, C(R¹³)(R¹⁴),N(Ar²), O, S, or Si(R¹³)(R¹⁴). Here, Ar² is the same as Ar¹ defined informula 1, and R¹³ and R¹⁴ are the same as in defined in formula 1.

When Ar¹ is

in formulas 2 and 3 above, the above formula 2 may be represented by thefollowing formula 4 and the above formula 3 may be represented by thefollowing formula 5.

In formulas 4 and 5 above, each of R¹ to R¹², L¹, X, Y and the like isthe same as defined in formula 1, and X¹ to X⁴ are each independently N,C or C(R¹³).

Preferably, at least one of X¹ to X⁴ is N and at least one of X¹ to X⁴is C boned to L, wherein R¹³ is the same as defined in formula 1. Z ringis a substituted or unsubstituted C₆-C₆₀ aromatic ring or a substitutedor unsubstituted C₂-C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P. Z ring may be preferably a C₆-C₁₈aromatic ring or a C₂-C₁₇ heterocyclic group, for example, benzene,naphthalene, phenanthrene, quinoline, quinoxaline, benzoquinoline,benzoquinoxaline, benzothiophene, dibenzothiophene, benzofuran,dibenzofuran, benzophenanthrothiophene, benzophenanthrofuran, and thelike.

Preferably, in formulas 4 and 5, Z ring may be represented by any one ofthe following formulas Z′-1 to Z′-9.

In formulas Z′-1 to Z′-9, “*” indicates the position fused with ringcontaining X¹ to X⁴, V is independently C(R¹³) or N, and W¹ and W² areeach independently a single bond, C(R¹³)(R¹⁴), N(Ar²), O, S, orSi(R¹³)(R¹⁴), wherein R¹³ and R¹⁴ are the same as defined in formula 1,and Ar² is the same as Ar¹ defined in formula 1.

Specifically, the compound represented by Formula 1 above may be one ofthe following compounds.

Preferably, at least one of R¹ to R¹² in formula 1 is-L′-N(R^(a))(R^(b)), and formula 1 may be represented by the followingformula 6.

In the above formula 6, each symbol of Ar¹, L¹, L′ X, Y, m, n, R^(a) andR^(b) and the like is the same as defined in formula 1, R²³ to R²⁵ arethe same as R¹ to R¹² defined in formula 1. p1 and p2 are each aninteger of 0 to 4, and a1 and a2 are each an integer of 0 to 4.

Preferably, in the above formula 6, a1 and a2 are each an integer of 0or 1, and a1+a2 is 1. That is, preferably, any one of R¹ to R¹² is-L′-N(R^(a))(R^(b)) and thus the above formula 6 may be represented byany one of the following formulas 6-1 to 6-4.

In formulas 6-1 to 6-4 above, R₁, R₂, R₃ and R₄ are each correspondingto R²³, R²⁴, R²⁴, R²⁵ of the above formula 6 and thus they are each thesame as R¹-R¹² defined in formula 1, p and s are each an integer of 0 to4 and q and r are each an integer of 0 to 2.

Specifically, the compound represented by the above Formula 6 may be anyone of the following compounds.

In another aspect of the present invention, the present inventionprovides an organic electric element comprising a first electrode, asecond electrode, and an organic material layer formed between the firstelectrode and the second electrode and comprising the compoundrepresented by formula 1. Here, the compound represented by formula 1may be comprised in at least one layer of a hole injection layer, a holetransport layer, an emission-auxiliary layer and a light emitting layer,and may be comprised in a single compound or as a component of a mixtureof two or more compounds.

That is, the compound represented by formula 1 may be used as materialof a hole injection layer, a hole transport layer, an emission-auxiliarylayer and/or a light emitting layer. Preferably, the compoundrepresented by formula 1 may be used as phosphorescent, more preferably,as red phosphorescent host of the light emitting layer.

In another embodiment of the present invention, the present inventionprovides a organic electric element further comprising a layer forimproving luminous efficiency formed on one side of the first electrodeand/or one side of the second electrode, the side facing the organicmaterial layer.

Hereinafter, synthesis method of the compound represented by Formula 1according to one embodiment of the present invention and preparationmethod of an organic electric element will be described in detail by wayof examples.

However, the present invention is not limited to the following examples.

Synthesis Example

Illustratively, the compound (final products) according to the presentinvention may be synthesized by reacting Core and Sub 1 as shown inReaction Scheme 1 or by reacting intermediate (C) and Sub 2 as shown inReaction Scheme 2, but there is no limitation thereto.

<Reaction Scheme 2> (X^(a)═Br, Cl or I, and symbol of each compound inthe following reaction scheme is the same as defined in formula 6.)

I. Synthesis of Core 1. Synthesis Example of Core (X^(a): Br, Cl or I)

Synthesis of Intermediate Core-II

(2-nitrophenyl)boronic acid substituted with R¹-R⁴ (1.1 eq.), Pd(PPh₃)₄(0.03 eq.), NaOH (3 eq.) and water (2.2 mL/1 mmol) were added to thesolution of Core-I (1 eq.) dissolved in THF (4.4 mL/1 mmol), and thenfollowed by stirring the mixture under heating and refluxing. When thereaction was completed, the reaction product was extracted with etherand water. And then the organic layer was dried with MgSO₄ andconcentrated. Then, the concentrate was separated by silica gel columnand recrystallized to obtain Core-II.

Synthesis of Core

Core-II (1 eq) obtained in the above synthesis and triphenylphosphine(2.5 eq) were dissolved in dichlorobenzene (4 mL/1 mmol), and then thesolution was heated and refluxed for 24 hours. When the reaction wascompleted, solvent was removed by distillation under reduced pressure,and then the residue was separated by silica gel column to obtain Coreof the product.

Synthesis of Core 1-1 (X═S)

Synthesis of Core 1-1-I

Triflic acid (246.1 ml, 2780.59 mmol) was added to2-bromo-6-(2-(methylsulfinyl)phenyl)naphthalene or6-bromo-1-(methylsulfinyl)-2-phenylnaphthalene) (64 g, 185.38 mmol), andthe mixture was stirred at room temperature. Subsequently, aqueoussolution of pyridine (3248 ml, pyridine:H₂O=1:5) was slowly addeddropwise, and followed by heating and refluxing the mixture for 30minutes. When the reaction was completed, the reaction product wasextracted with CH₂Cl₂ and water. And then, the organic layer was driedwith MgSO₄ and concentrated. Then, the concentrate was separated bysilica gel column and recrystallized to obtain 49.93 g (yield: 86%) ofthe product.

Synthesis of Intermediate Core 1-1-II

2-nitrophenyl)boronic acid (28.25 g, 169.24 mmol), Pd(PPh₃)₄ (5.33 g,4.62 mmol), NaOH (18.46 g, 461.58 mmol) and water (338 ml) were added tothe solution of Core 1-1-I (48.19 g, 153.86 mmol) dissolved in THF (677ml), and then followed by string the mixture under heating andrefluxing. When the reaction was completed, the reaction product wasextracted with ether and water. And then, the organic layer was driedwith MgSO₄ and concentrated. Then, the concentrate was separated bysilica gel column and then recrystallized to obtain 48.67 g (yield: 89%)of the product.

Synthesis of Core 1-1

Core 1-1-II (48.67 g, 136.94 mmol) obtained in the above synthesis andtriphenylphosphine (89.80 g, 342.35 mmol) were dissolved ino-dichlorobenzene (548 ml), and then the mixture was heated and refluxedfor 24 hours. When the reaction is completed, solvent was removed bydistillation under reduced pressure, and then the residue was separatedby silica gel column to obtain 20.82 g (yield: 47%) of the product.

Synthesis of Core 1-7

Synthesis of Core 1-7-I

48.19 g (yield: 83%) of the product was obtained by reacting thestarting material 6-bromo-1-(2-(methyl sulfinyl)phenyl)naphthalene or6-bromo-2-(methyl sulfinyl)-1-phenylnaphthalene (64 g, 185.37 mmol),triflic acid (246 ml, 2780.59 mmol) and aqueous solution of pyridine(3248 ml, pyridine:H₂O=1:5) by the same method as in synthesis exampleof Core 1-1-I.

Synthesis of Intermediate Core 1-7-II

47.57 g (yield: 87%) of the product was obtained by reacting Core 1-7-I(48.19 g, 153.86 mmol) obtained in the above synthesis, THF (677 ml),(2-nitrophenyl)boronic acid (28.25 g, 169.24 mmol), Pd(PPh₃)₄ (5.33 g,4.62 mmol), NaOH (18.46 g, 461.58 mmol) and water (338 ml) by the samemethod as in synthesis example of Core 1-1-II.

Synthesis of Intermediate Core 1-7

19.93 g (yield: 45%) of the product was obtained by reacting Core 1-7-II(48.67 g, 136.94 mmol) obtained in the above synthesis,triphenylphosphine (89.80 g, 342.35 mmol) and o-dichlorobenzene (548 ml)by the same method as in synthesis example of Core 1-1.

Synthesis of Core 1-2

Synthesis of Intermediate Core 1-2-II

32.31 g (yield: 78%) of the product was obtained by reacting Core 1-1-I(30 g, 95.78 mmol), THF (421 ml),(2-nitro-5-(pyridin-2-yl)phenyl)boronic acid (25.71 g, 105.36 mmol),Pd(PPh₃)₄ (3.32 g, 2.87 mmol), NaOH (11.49 g, 287.35 mmol) and water(211 ml) by the same method as in synthesis example of Core 1-1-II.

Synthesis of Core 1-2

12.57 g (yield: 42%) of the product was obtained by reacting Core 1-2-II(32.31 g, 74.71 mmol), triphenylphosphine (48.99 g, 186.77 mmol) ando-dichlorobenzene (299 ml) by the same method as in synthesis example ofCore 1-I.

Synthesis of Core 1-4

Synthesis of Intermediate Core 1-4-II

30.38 g (yield: 84%) of the product was obtained by reacting Core 1-4-I(30 g, 83.29 mmol), THF (366 ml), (5-bromo-2-nitrophenyl)boronic acid(22.52 g, 91.61 mmol), Pd(PPh₃)₄ (2.89 g, 2.5 mmol), NaOH (9.99 g,249.85 mmol) and water (183 ml) by the same method as in synthesisexample of Core 1-1-II.

Synthesis of Intermediate Core 1-4-III

12.57 g (yield: 42%) of the product was obtained by reacting Core 1-4-II(32.31 g, 74.71 mmol), triphenylphosphine (48.99 g, 186.77 mmol) ando-dichlorobenzene (299 ml) by the same method as in synthesis example ofCore 1-1.

Synthesis of Core 1-4

15.35 g (yield: 87%) of the product was obtained by reacting Core1-4-III (12.57 g, 31.25 mmol), THF (138 ml),(9-phenyl-9H-carbazol-3-yl)boronic acid (9.87 g, 34.37 mmol), Pd(PPh₃)₄(1.08 g, 0.94 mmol), NaOH (3.75 g, 93.73 mmol) and water (68 ml) by thesame method as in synthesis example of Core 1-I-II.

Synthesis of Core 1-8

Synthesis of Intermediate Core 1-8-II

29.83 g (yield: 83%) of the product was obtained by reacting Core 1-4-I(30 g, 83.29 mmol), THF (366 ml), (4-nitro-[1,1′-biphenyl]-3-yl)boronicacid (22.26 g, 91.61 mmol), Pd(PPh₃)₄ (2.89 g, 2.5 mmol), NaOH (9.99 g,249.85 mmol) and water (183 ml) by the same method as in synthesisexample of Core 1-1-II.

Synthesis of Core 1-8

11.88 g (yield: 43%) of the product was obtained by reacting Core 1-8-II(29.83 g, 69.13 mmol), triphenylphosphine (45.33 g, 172.82 mmol) ando-dichlorobenzene (277 ml) by the same method as in synthesis example ofCore 1-1.

Synthesis of Core 1-13 (X═O)

Synthesis of Intermediate Core 1-13-I

6-bromo-2-phenylnaphthalen-1-ol (200 g, 668.54 mmol), palladium acetate(1.5 g, 6.69 mmol) and 3-nitropyridine (165.93 g, 1337.08 mmol) weredissolved in the mixed solvent (C₆H₆:DMI=3:2). Then, BzOOt-Bu (1.30 g,6.69 mmol) was added to the solution and followed by stirring themixture at 90° C. for 4 hours. When the reaction was completed, thereaction product was extracted with CH₂Cl₂ and water. Then, the organiclayer was dried with MgSO₄ and concentrated under reduced pressure.Then, the concentrate was separated by silica gel column and thenrecrystallized to obtain 89.40 g (yield: 45%) of the product.

Synthesis of Intermediate Core 1-13-II

47.39 g (yield: 83%) of the product was obtained by reacting Core 1-13-I(50 g, 168.27 mmol), THF (740 ml), (2-nitrophenyl)boronic acid (30.90 g,185.09 mmol), Pd(PPh₃)₄ (5.83 g, 5.05 mmol), NaOH (20.19 g, 504.80 mmol)and water (370 ml) by the same method as in synthesis example of Core1-1-II.

Synthesis of Core 1-13

18.89 g (yield: 44%) of the product was obtained by reacting Core1-13-II (47.39 g 139.65 mmol), triphenylphosphine (91.57 g, 349.13 mmol)and o-dichlorobenzene (559 ml) by the same method as in synthesisexample of Core 1-1.

Synthesis of Core 1-18

Synthesis of Intermediate Core 1-18-I

78.67 g (yield: 44%) of the product was obtained by reacting2-(6-bromonaphthalen-1-yl)phenol or 6-bromo-1-phenylnaphthalen-2-ol (180g, 601.69 mmol), Palladium acetate (1.35 g, 6.02 mmol), 3-nitropyridine(149.34 g, 1203.37 mmol) and BzOOt-Bu (1.17 g, 6.02 mmol) by the samemethod as in synthesis example of intermediate Core 1-13-I.

Synthesis of Intermediate Core 1-18-II

48.53 g (yield: 85%) of the product was obtained by reacting Core 1-18-I(50 g, 168.27 mmol), THF (740 ml), (2-nitrophenyl)boronic acid (30.90 g,185.09 mmol), Pd(PPh₃)₄ (5.83 g, 5.05 mmol), NaOH (20.19 g, 504.80 mmol)and water (370 ml) by the same method as in synthesis example of Core1-1-II.

Synthesis of Core 1-18

18.46 g (yield: 42%) of the product was obtained by reacting Core1-18-II (48.53 g 143.01 mmol), triphenylphosphine (93.78 g, 357.53 mmol)and o-dichlorobenzene (572 ml) by the same method as in synthesisexample of Core 1-1.

Synthesis of Core 1-21

Synthesis of Intermediate Core 1-21-II

46.52 g (yield: 71%) of the product was obtained by reacting Core 1-18-I(50 g, 168.27 mmol), THF (740 ml), (2-nitronaphthalen-1-yl)boronic acid(40.16 g, 185.09 mmol), Pd(PPh₃)₄ (5.83 g, 5.05 mmol), NaOH (20.19 g,504.80 mmol) and water (370 ml) by the same method as in synthesisexample of Core 1-1-II.

Synthesis of Core 1-21

17.49 g (yield: 41%) of the product was obtained by reacting Core1-21-II (46.52 g, 119.47 mmol), triphenylphosphine (78.34 g, 298.67mmol) and o-dichlorobenzene (478 ml) by the same method as in synthesisexample of Core 1-1.

Synthesis of Core 1-24

Synthesis of Intermediate Core 1-24-I(1)

(6-bromonaphthalen-2-yl)boronic acid (189.57 g, 755.61 mmol), Pd(PPh₃)₄(23.81 g, 20.61 mmol), K₂CO₃ (284.82 g, 2060.75 mmol) and water (1511ml) were added to the solution of methyl 2-iodobenzoate (180 g, 686.92mmol) dissolved in THF (3022 ml) and then followed by stirring themixture at 80° C. When the reaction was completed, the reaction productwas extracted with CH₂Cl₂ and water. And then, the organic layer wasdried with MgSO₄ and concentrated. Then, the concentrate was separatedby silica gel column and then recrystallized to obtain 175.78 g (yield:75%) of the product.

Synthesis of Intermediate Core 1-24-II(2)

Core 1-24-I(1) (120 g, 351.7 mmol) obtained in the above synthesis wasdissolved in methanesulfonic acid (1143 ml), and then followed bystirring the mixture at 50˜60° C. When the reaction was completed, theresultant was cooled to 0° C. and water was added to the resultant inorder to obtain precipitate. The precipiated solid was filtered andwashed with a small amount of water. Then, the filtered solid wasdissolved in CH₂Cl₂ and the solution was dried with MgSO₄ andconcentrated. The concentrate was separated by silica gel column andrecrystallized to obtain 50.02 g (yield: 46%) of the product.

Synthesis of Intermediate Core 1-24-I(3)

Core 1-24-I(2)(60 g, 194.07 mmol) obtained in the above synthesis wasdissolved in ethylene glycol (776 ml), and hydrazine monohydrate (291.46g, 5822.23 mmol) and KOH (27.22 g, 485.19 mmol) were added to thesolution. Then, the mixture was stirred at 185° ° C. When the reactionwas completed, the resultant was cooled to 0° C. and water was added tothe resultant in order to obtain precipitate. The precipiated solid wasfiltered and washed with a small amount of water.

Then, the filtered solid was dissolved in CH₂Cl₂ and the solution wasdried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column and recrystallized to obtain 26.35 g (yield: 46%) ofthe product.

Synthesis of Core 1-24-I

n-BuLi (64.7 ml, 161.73 mmol) was added to the solution of Core1-24-I(3) (50 g, 161.73 mmol) dissolved in THF (647 ml) at −78° C., andthe mixture was stirred at room temperature for 1 hour. After themixture was cooled to −78° C., CH₃I (57.39 g, 404.32 mmol) was added.Then, the mixture was stirred at room temperature for 3 hours. When thereaction was completed, water was added to the reaction product and thenfollowed by extracting the mixture with diethyl ether. And then, theorganic layer was dried with MgSO₄ and concentrated under reducedpressure. Then, the concentrate was separated by silica gel columnapplied ethyl acetate and n-hexan to obtain 20.05 g (yield: 42%) of theproduct.

Synthesis of Intermediate Core 1-24-II

17.45 g (yield: 77%) of the product was obtained by reacting Core 1-24-I(20.05 g, 62.03 mmol), THF (273 ml), (2-nitrophenyl)boronic acid (11.39g, 68.23 mmol), Pd(PPh₃)₄ (2.15 g, 1.86 mmol), NaOH (7.44 g, 186.09mmol) and water (136 ml) by the same method as in synthesis example ofCore 1-1-II.

Synthesis of Core 1-24

6.85 g (yield: 43%) of the product was obtained by reacting Core 1-24-II(17.45 g, 47.75 mmol), triphenylphosphine (31.31 g, 119.38 mmol) ando-dichlorobenzene (191 ml) by the same method as in synthesis example ofCore 1-1.

Synthesis of Core 1-27

Synthesis of Intermediate Core 1-27-I(1)

(6-bromonaphthalen-2-yl)boronic acid (189.57 g, 755.61 mmol), Pd(PPh3)4(23.81 g, 20.61 mmol), K2CO3 (284.82 g, 2060.75 mmol) and water (1511ml) were added to the solution of methyl 2-iodobenzoate (180 g, 686.92mmol) dissolved in THF (3022 ml). Then the mixture was stirred at 80° C.When the reaction was completed, the reaction product was extracted withCH₂Cl₂ and water. And then, the organic layer was dried with MgSO₄ andconcentrated. Then the concentrate was separated by silica gel columnand recrystallized to obtain 180.47 g (yield: 77%) of the product.

Synthesis of Intermediate Core 1-27-I(2)

Core 1-27-I(1) (120 g, 351.7 mmol) obtained in the above synthesis wasdissolved in methanesulfonic acid (1143 ml) and the solution was stirredat 50˜60° C. When the reaction was completed, the resultant was cooledto 0° C. and water was added to the resultant in order to obtainprecipitate. The precipiated solid was filtered and washed with a smallamount of water. Then, the filtered solid was dissolved in CH₂Cl₂ andthe solution was dried with MgSO₄ and concentrated. The concentrate wasseparated by silica gel column and recrystallized to obtain 46.75 g(yield: 43%) of the product.

Synthesis of Intermediate Core 1-27-I(3)

Core 1-27-I(2) (60 g, 194.07 mmol) obtained in the above synthesis wasdissolved in ethylene glycol (776 ml), and hydrazine monohydrate (291.46g, 5822.23 mmol) and KOH (27.22 g, 485.19 mmol) were added to thesolution. Then the mixture was stirred at 185° ° C. When the reactionwas completed, the resultant was cooled to 0° C. and water was added tothe resultant in order to obtain precipitate. The precipiated solid wasfiltered and washed with a small amount of water. Then, the filteredsolid was dissolved in CH₂Cl₂ and the solution was dried with MgSO₄ andconcentrated. The concentrate was separated by silica gel column andrecrystallized to obtain 26.92 g (yield: 47%) of the product.

Synthesis of Core 1-27-I

n-BuLi (64.7 ml, 161.73 mmol) was added to the solution of Core1-27-I(3) (50 g, 161.73 mmol) dissolved in THF (647 ml) at −78° C., andthe mixture was stirred at room temperature for 1 hour. After themixture was cooled to −78° C., CH₃I (57.39 g, 404.32 mmol) was added.Then, the mixture was stirred at room temperature for 3 hours. When thereaction was completed, water was added to the reaction product and thenfollowed by extracting the mixture with diethyl ether. And then, theorganic layer was dried with MgSO₄ and concentrated under reducedpressure. Then, the concentrate was separated by silica gel columnapplied ethyl acetate and n-hexan to obtain 19.57 g (yield: 41%) of theproduct.

Synthesis of intermediate Core 1-27-II

14.80 g (yield: 75%) of the product was obtained by reacting Core 1-27-I(17.45 gg, 53.99 mmol), THF (238 ml), (2-nitrophenyl)boronic acid (9.91g, 59.39 mmol), Pd(PPh₃)₄ (1.87 g, 1.62 mmol), NaOH (6.48 g, 161.96mmol) and water (119 ml) by the same method as in synthesis example ofCore 1-1-II.

Synthesis of Core 1-27

5.94 g (yield: 44%) of the product was obtained by reacting Core 1-24-II(14.80 g, 40.50 mmol), triphenylphosphine (26.56 g, 101.25 mmol) ando-dichlorobenzene (162 ml) by the same method as in synthesis example ofCore 1-1.

2. Synthesis Example of Intermediate (C)

Synthesis of 1-1-1(C)

Synthesis of 1-1-1

After mixing Core 1-1 (100 g, 309.21 mmol), iodobenzene (63.08 g, 309.21mmol), Pd₂(dba)₃ (14.16 g, 15.46 mmol), P(t-Bu)₃ (6.26 g, 30.92 mmol),NaOt-Bu (44.57 g, 463.81 mmol) and toluene (3246 mL), the mixed reactionsolution was stirred at 100° C. When the reaction was completed, thereaction product was extracted with ether and water. And then, theorganic layer was dried with MgSO₄ and concentrated. Then, theconcentrate was separated by silica gel column and recrystallized toobtain 107.47 g (yield: 87%) of the product.

Synthesis of 1-1-1(A)

Compound 1-1-1 (100 g, 250.31 mmol) obtained in the above synthesis,NBS(N-bromosuccinimide)(93.6 g, 525.64 mmol) and BPO(benzoylperoxide)(6.1 g, 25.03 mmol) were dissolved in CH₂Cl₂ (751 ml),and the mixture was stirred at room temperature for 3 hours. When thereaction was completed, aqueous solution of sodium bicarbonate was addedto the reaction product. Then, the mixture was stirred for 30 minutesand extracted with CH₂Cl₂. And then the organic layer was dried withanhydrous MgSO₄, filtered under reduced pressure and concentrated underreduced pressure. Then, the concentrate was separated by silica gelcolumn to obtain 77.84 g (yield: 65%) of the product.

Synthesis of 1-1-1(B)

Compound 1-1-1(A)(40 g, 83.6 mmol) obtained in the above synthesis wasdissolved in anhydrous ether (293 ml), and n-BuLi (36.8 ml, 92 mmol) wasslowly added to the solution at −78° C. Then the mixture was stirred atroom temperature for 1 hour. After the mixture was cooled to −78° C.,triisopropyl borate was added to the mixture. Then, the reactionsolution was warmed gradually to room temperature and diluted withwater. Then, HCl (2N) was added to the diluted reaction solution andfollowed by stirring the mixture. When the reaction was completed, thereaction product was extracted with ethyl acetate and water. Then theorganic layer was dried with MgSO₄ and concentrated. Then, theconcentrate was separated by silica gel column and recrystallized toobtain 25.58 g (yield: 69%) of the product.

Synthesis of 1-1-1(C)

23.04 g (yield: 72%) of the product was obtained by reacting Core1-1-1(B) (25.58 g, 57.70 mmol), THF (254 ml), 1,3-dibromobenzene (13.61g, 57.70 mmol), Pd(PPh₃)₄ (2.00 g, 1.73 mmol), K₂CO₃ (23.92 g, 173.10mmol) and water (127 ml) by the same method as in synthesis example ofCore 1-24-I(1).

Synthesis of 1-1-1(D)

21.05 g (yield: 74%) of the product was obtained by reacting Core1-1-1(B) (20 g, 45.11 mmol), THF (199 ml), 4′-bromo-3-iodo-1,1′-biphenyl(16.20 g, 45.11 mmol), Pd(PPh₃)₄ (1.56 g, 1.35 mmol), K₂CO₃ (18.71 g,135.34 mmol) and water (99.25 ml) by the same method as in synthesisexample of Core 1-24-I(1).

Synthesis of 1-2-1(C)

Synthesis of 1-2-1

103.77 g (yield: 84%) of the product was obtained by reacting Core 1-7(100 g, 309.21 mmol), iodobenzene (63.08 g, 309.21 mmol), Pd₂(dba)₃(14.16 g, 15.46 mmol), P(t-Bu)₃ (6.26 g, 30.92 mmol), NaOt-Bu (44.57 g,463.81 mmol) and toluene (3246 mL) by the same method as in synthesisexample of 1-1-1.

Synthesis of 1-2-1(A)

36.14 g (yield: 62%) of the product was obtained by reacting Compound1-2-1 (50 g, 105.13 mmol), NBS (39.3 g, 220.77 mmol), BPO (2.5 g, 10.51mmol) and CH₂Cl₂ (315 ml) by the same method as in synthesis example of1-1-1(A).

Synthesis of 1-2-1(B)

22 g (yield: 65%) of the product was obtained by reacting 1-2-1(A)(36.14g, 65.2 mmol) obtained in the above synthesis, anhydrous Ether 228 ml,2.5 M concentration of n-BuLi (28.68 ml, 71.7 mmol) and Tri isopropylborate (18.39 g, 97.76 mmol) by the same method as in synthesis exampleof 1-1-1(B).

Synthesis of 1-2-1(C)

20.73 g (yield: 69%) of the product was obtained by reacting 1-2-1(B)(22 g, 42.35 mmol), THF (186 ml), 1,3,5-tribromobenzene (13.33 g, 42.35mmol), Pd(PPh₃)₄ (1.47 g, 1.27 mmol), K₂CO₃ (17.56 g, 127.06 mmol) andwater (93 ml) by the same method as in synthesis example of 1-1-1(C).

Synthesis of 2-1-2(B)

Synthesis of 2-1-2

128.59 g (yield: 86%) of the product was obtained by reacting Core 1-13(100 g, 325.37 mmol), 3-iodo-1,1′-biphenyl (91.14 g, 325.37 mmol),Pd₂(dba)₃ (14.90 g, 16.27 mmol), P(t-Bu)₃ (6.58 g, 32.54 mmol), NaOt-Bu(46.90 g, 488.06 mmol) and toluene (3416 mL) by the same method as insynthesis example of 1-1-1.

Synthesis of 2-1-2(A)

36.17 g (yield: 60%) of the product was obtained by reacting compound2-1-1 (50 g, 130.4 mmol), NBS (48.74 g, 273.84 mmol), BPO (3.16 g, 13.04mmol) and CH₂Cl₂ (391 ml) by the same method as in synthesis example of1-1-1(A).

Synthesis of 2-1-2(B)

20.73 g (yield: 69%) of the product was obtained by reacting 2-1-2(A)(36.17 g, 78.23 mmol), THF (186 ml), (4-bromophenyl)boronic acid (13.33g, 42.35 mmol), Pd(PPh₃)₄ (1.47 g, 1.27 mmol), K₂CO₃ (17.56 g, 127.06mmol) and water (93 ml) by the same method as in synthesis example of1-1-1(C).

Synthesis of 2-1-2(C)

Synthesis of 3-1-1

70.50 g (yield: 82%) of the product was obtained by reacting Core 1-24(70 g, 209.94 mmol), iodobenzne (420.83 g, 209.94 mmol), Pd₂(dba)₃ (9.61g, 10.5 mmol), P(t-Bu)₃ (4.25 g, 20.99 mmol), NaOt-Bu (30.26 g, 314.91mmol) and toluene (2204 mL) by the same method as in synthesis exampleof 1-1-1.

Synthesis of 3-1-1(A)

41.50 g (yield: 58%) of the product was obtained by reacting compound3-1-1 (60 g, 146.51 mmol) obtained in the above synthesis, NBS (54.76 g,307.68 mmol), BPO (3.55 g, 14.65 mmol) and CH₂Cl₂ (439 ml) by the samemethod as in synthesis example of 1-1-1(A).

Synthesis of 3-1-1(B)

23.11 g (yield: 60%) of the product was obtained by reacting3-1-1(A)(41.50 g, 84.97 mmol) obtained in the above synthesis, anhydrousEther 297 ml, 2.5 M concentration of n-BuLi (37.38 ml, 93.46 mmol) andtriisopropyl borate (23.97 g, 127.45 mmol) by the same method as insynthesis example of 1-1-1(B).

Synthesis of 3-1-1(C)

22.91 g (yield: 67%) of the product was obtained by reacting 3-1-1(B)(23.11 g, 50.98 mmol), THF (224 ml), 3,7-dibromodibenzo[b,d]thiophene(17.44 g, 50.98 mmol), Pd(PPh₃)₄ (1.77 g, 1.53 mmol), K₂CO₃ (21.14 g,152.93 mmol) and water (112 ml) by the same method as in synthesisexample of 1-1-1(C).

Synthesis of 3-2-1(C)

Synthesis of 3-2-1

68.78 g (yield: 80%) of the product was obtained by reacting Core 1-27(70 g, 209.94 mmol), iodobenzne (42.83 g, 209.94 mmol), Pd₂(dba)₃ (9.61g, 10.5 mmol), P(t-Bu)₃ (4.25 g, 20.99 mmol), NaOt-Bu (30.26 g, 314.91mmol) and toluene (2204 mL) by the same method as in synthesis exampleof 1-1-1.

Synthesis of 3-2-1(A)

40.07 g (yield: 56%) of the product was obtained by reacting compound3-2-1 (60 g, 146.51 mmol) obtained in the above synthesis, NBS (54.76 g,307.68 mmol), BPO (3.55 g, 14.65 mmol) and CH₂Cl₂ (439 ml) by the samemethod as in synthesis example of 1-1-1(A).

Synthesis of 3-2-1(B)

23.06 g (yield: 62%) of the product was obtained by reacting3-2-1(A)(40.07 g, 82.04 mmol) obtained in the above synthesis, anhydrousEther 287 ml, 2.5 M concentration of n-BuLi (36.1 ml, 90.24 mmol) andtriisopropyl borate (23.14 g, 123.06 mmol) by the same method as insynthesis example of 1-1-1(B).

Synthesis of 3-2-1(C)

22.17 g (yield: 65%) of the product was obtained by reacting3-2-1(B)(23.06 g, 50.87 mmol), THF (223 ml),4′-bromo-3-iodo-1,1′-biphenyl (17.40 g, 50.87 mmol), Pd(PPh₃)₄ (1.76 g,1.53 mmol), K₂CO₃ (21.09 g, 152.60 mmol) and water (111 ml) by the samemethod as in synthesis example of 1-1-1(C).

TABLE 1 FD-MS of Core intermediates compound FD-MS compound FD-MS1-1-1(A) m/z = 477.02(C₂₈H₁₆BrNS = 478.40) 1-1-1(B) m/z =443.12(C₂₈H₁₈BNO₂S = 443.32) 1-1-1(C) m/z = 553.05(C₃₄H₂₀BrNS = 554.50)1-1-1(D) m/z = 629.08(C₄₀H₂₄BrNS = 630.59) 1-2-1(A) m/z =477.02(C₂₈H₁₆BrNS = 478.40) 1-2-1(B) m/z = 443.12(C₂₈H₁₈BNO₂S = 443.32)1-2-1(C) m/z = 630.96(C₃₄H₁₉Br₂NS = 633.39) 2-1-2(A) m/z =537.07(C₃₄H₂₀BrNO = 538.43) 2-1-2(B) m/z = 613.10(C₄₀H₂₄BrNO = 614.53)3-1-1(A) m/z = 487.09(C₃₁H₂₂BrN = 488.42) 3-1-1(B) m/z =453.19(C₃₁H₂₄BNO₂ = 453.34) 3-1-1(C) m/z = 669.11(C₄₃H₂₈BrNS = 670.66)3-2-1(A) m/z = 487.09(C₃₁H₂₂BrN = 488.42) 3-2-1(B) m/z =453.19(C₃₁H₂₄BNO₂ = 453.34) 3-2-1(C) m/z = 639.16(C₄₃H₃₀BrN = 640.61)

Example of Core 1

TABLE 2 FD-MS of Core compound FD-MS compound FD-MS Core 1-1 m/z =323.08(C₂₂H₁₃NS = 323.41) Core 1-2 m/z = 400.10(C₂₇H₁₆N₂S = 400.49) Core1-3 m/z = 475.14(C₃₄H₂₁NS = 475.60) Core 1-4 m/z = 564.17(C₄₀H₂₄N₂S =564.70) Core 1-5 m/z = 423.11(C₃₀H₁₇NS = 423.53) Core 1-6 m/z =720.17(C₅₀H₂₈N₂S₂ = 720.90) Core 1-7 m/z = 323.08(C₂₂H₁₃NS = 323.41)Core 1-8 m/z = 399.11(C₂₈H₁₇NS = 399.51) Core 1-9 m/z = 400.10(C₂₇H₁₆N₂S= 400.49) Core 1-10 m/z = 564.17(C₄₀H₂₄N₂S = 564.70) Core 1-11 m/z =373.09(C₂₆H₁₅NS = 373.47) Core 1-12 m/z = 720.17(C₅₀H₂₈N₂S₂ = 720.90)Core 1-13 m/z = 307.10(C₂₂H₁₃NO = 307.34) Core 1-14 m/z =459.16(C₃₄H₂₁NO = 459.54) Core 1-15 m/z = 384.13(C₂₇H₁₆N₂O = 384.43)Core 1-16 m/z = 688.22(C₅₀H₂₈N₂O₂ = 688.77) Core 1-17 m/z =357.12(C₂₆H₁₅NO = 357.40) Core 1-18 m/z = 307.10(C₂₂H₁₃NO = 307.34) Core1-19 m/z = 383.13(C₂₈H₁₇NO = 383.44) Core 1-20 m/z = 384.13(C₂₇H₁₆N₂O =384.43) Core 1-21 m/z = 357.12(C₂₆H₁₅NO = 357.40) Core 1-22 m/z =548.19(C₄₀H₂₄N₂O = 548.63) Core 1-23 m/z = 688.22(C₅₀H₂₈N₂O₂ = 688.77)Core 1-24 m/z = 333.15(C₂₅H₁₉N = 333.43) Core 1-25 m/z = 485.21(C₃₇H₂₇N= 485.62) Core 1-26 m/z = 740.32(C₅₆H₄₀N₂ = 740.93) Core 1-27 m/z =333.15(C₂₅H₁₉N = 333.43) Core 1-28 m/z = 740.32(C₅₆H₄₀N₂ = 740.93) Core1-29 m/z = 349.13(C₂₄H₁₉NSi = 349.50) Core 1-30 m/z = 349.13(C₂₄H₁₉NSi =349.50) Core 1-31 m/z = 473.16(C₃₄H₂₃NSi = 473.64)

II. Synthesis of Sub 1

Synthesis of Sub 1-12

Phenylboronic acid pinacol ester (22.3 g, 109 mmol), THF (240 ml),2,4,6-trichloropyrimidine (10 g, 54.5 mmol), Pd(PPh₃)₄ (3.8 g, 3.27mmol), K₂CO₃ (45.2 g, 327 mmol), water (120 ml) were mixed, and then themixed solution was stirred at 90° C. When the reaction was completed,the reaction product was extracted with CH₂Cl₂ and water. And then, theorganic layer was dried with MgSO₄ and concentrated. Then, theconcentrate was separated by silica gel column and recrystallized toobtain 9.5 g (yield: 65%) of the product.

Synthesis of Sub 1-14

Synthesis of Sub 1-I-14

The mixture of 2-aminobenzoic acid (15.22 g, 111 mmol) and urea (46.66g, 776.9 mmol) was stirred at 160° C. After the progress of reaction wasconfirmed by TLC, the reaction solution was cooled to 100° C. Then,water (55 ml) was added to the reaction solution and the mixture wasstirred for 1 hour. When the reaction was completed, the produced solidwas filtered under reduced pressure, washed with water, and dried toobtain 14.58 g (yield: 81%) of the product.

Synthesis of Sub 1-II-14

Sub 1-I-14 (14.58 g, 89.9 mmol) obtained in the above synthesis wasdissolved in POCl₃ (60 ml). Then, N,N-Diisopropylethylamine (29.05 g,224.8 mmol) was slowly added to the solution and the mixture was stirredat 90° C. When the reaction was completed, the reaction product wasconcentrated. Then, ice water (120 ml) was added to the reaction productand the reaction product was stirred at room temperature for 1 hour.Then, the produced solid was filtered under reduced pressure and driedto obtain 15.39 g (yield: 86%) of the product.

Synthesis of Sub 1-14

9.64 g (yield: 49%) of the product was obtained by reactingphenylboronic acid pinacol ester (19.2 g, 75.4 mmol), THF (332 ml),2,4-dichloroquinazoline (15 g, 75.4 mmol), Pd(PPh₃)₄ (2.6 g, 2.26 mmol),K₂CO₃ (31.2 g, 226 mmol) and water (166 ml) by the same method as insynthesis example of Sub 1-12.

Synthesis of Sub 1-28

Synthesis of Sub 1-I-28

41.94 g (yield: 63%) of the product was obtained by reacting10-aminophenanthrene-9-carboxylic acid (60.22 g, 253.8 mmol), urea(106.71 g, 1776.8 mmol) and water (130 ml) by the same method as insynthesis example of Sub 1-I-14.

Synthesis of Sub 1-II-28

40.19 g (yield: 84%) of the product was obtained by reacting Sub 1-II-28(41.94 g, 159.9 mmol) obtained in the above synthesis, POCl₃ (110 ml)and N,N-Diisopropylethylamine (51.67 g, 399.8 mmol) by the same methodas in synthesis example of Sub 1-11-14.

Synthesis of Sub 1-28

23.81 g (yield: 52%) of the product was obtained by reacting Sub 1-I-28(40.19 g, 134.3 mmol) obtained in the above synthesis,4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (30.16 g, 147.8 mmol),Pd(PPh₃)₄ (6.21 g, 5.4 mmol), K₂CO₃ (55.7 g, 403 mmol), THF and water bythe same method as in synthesis example of Sub 1-14.

Synthesis of Sub 1-36

9.21 g (yield: 44%) of the product was obtained by reactingphenylboronic acid pinacol ester (14.4 g, 70.6 mmol), THF (310 ml),2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (18 g, 70.6 mmol),Pd(PPh₃)₄ (2.4 g, 2.1 mmol), K₂CO₃ (29.3 g, 212 mmol) and water (155 ml)by the same method as in synthesis example of Sub 1-14.

Example of Sub 1

TABLE 3 FD-MS of Sub 1 compound FD-MS compound FD-MS Sub 1-3 m/z =231.99(C₁₂H₉Br = 233.10) Sub 1-6 m/z = 272.02(C₁₅H₁₃Br = 273.17) Sub1-11 m/z = 245.97(C₁₂H₇BrO = 247.09) Sub 1-12 m/z = 266.06(C₁₆H₁₁ClN₂ =266.72) Sub 1-21 m/z = 416.11(C₂₈H₁₇ClN₂ = 416.90) Sub 1-34 m/z =446.06(C₂₈H₁₅ClN₂S = 446.95) Sub 1-49 m/z = 450.04(C₂₆H₁₅BrN₂O = 451.31)Sub 1-74 m/z = 400.02(C₂₂H₁₃BrN₂O = 401.26) Sub 1-78 m/z =346.03(C₂₀H₁₁ClN₂S = 346.83) Sub 1-90 m/z = 339.86(C₁₂H₆Br₂S = 342.05)

III. Synthesis Example of Sub 2

Sub 2 of reaction scheme 2 may be synthesized according to, but notlimited to, the following reaction scheme.

<Reaction Scheme 3> (Here, Hal is Br or Cl)

Synthesis of Sub 2-4

The reaction solution mixed with 4-Aminobiphenyl(5.23 g, 30.9 mmol),4-Bromobiphenyl(7.2 g, 30.9 mmol), Pd₂(dba)₃ (1.41 g, 1.54 mmol),P(t-Bu)₃ (0.62 g, 3.1 mmol), NaOt-Bu (8.91 g, 92.7 mmol) and toluene(324 mL) was stirred at 100° C. for 24 hours under refluxing. When thereaction was completed, the reaction product was extracted with etherand water. And then, the organic layer was dried with MgSO₄ andconcentrated. Then, the concentrate was separated by silica gel columnand recrystallized to obtain 6.75 g (yield: 68%) of the product.

Synthesis of Sub 2-11

12.1 g (yield: 77%) of the product was obtained by reacting2-bromodibenzo[b,d]thiophene (15 g, 57 mmol), aniline (5.31 g, 57 mmol),Pd₂(dba)₃ (2.61 g, 2.85 mmol), P(t-Bu)₃ (1.15 g, 5.7 mmol), NaOt-Bu(16.4 g, 171 mmol) and toluene (598 mL) by the same method as insynthesis example of Sub 2-4.

Synthesis of Sub 2-16

8.07 g (yield: 80%) of the product was obtained by reacting the startingmaterial 3-bromodibenzo[b,d]furan (8.06 g, 32.6 mmol),naphthalen-1-amine (9.34 g, 65.2 mmol), Pd₂(dba)₃ (0.9 g, 1 mmol), 50%P(t-Bu)₃ (1.3 ml, 2.6 mmol), NaOt-Bu (9.41 g, 97.9 mmol) and toluene bythe same method as in synthesis example of Sub 2-4.

Synthesis of Sub 2-9

11.73 g (yield: 82%) of the product was obtained by reacting thestarting material 2-bromo-9,9-dimethyl-9H-fluorene (10.81 g, 39.6 mmol),[1,1′-biphenyl]-4-amine (13.39 g, 79.1 mmol), Pd₂(dba)₃ (1.09 g, 1.2mmol), 50% P(t-Bu)₃ (1.5 ml, 3.2 mmol), NaOt-Bu (11.41 g, 118.7 mmol)and toluene by the same method as in synthesis example of Sub 2-4.

TABLE 4 FD-MS of Sub 2 compound FD-MS compound FD-MS Sub 2-4 m/z =321.15(C₂₄H₁₉N = 321.41) Sub 2-6 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 2-9m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 2-11 m/z = 275.08(C₁₈H₁₃NS = 275.37)Sub 2-12 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-15 m/z = 259.10(C₁₈H₁₃NO= 259.30) Sub 2-16 m/z = 309.12(C₂₂H₁₅NO = 309.36) Sub 2-18 m/z =385.15(C₂₈H₁₉NO = 385.46) Sub 2-26 m/z = 384.16(C₂₈H₂₀N₂ = 384.47)

Example of Sub 2

IV. Final Product(1)

Synthesis of 1-1-5

The reaction solution mixed with Core 1-1 (5.4 g, 16.7 mmol), Sub 1-6(4.56 g, 16.7 mmol), Pd₂(dba)₃ (0.76 g, 0.84 mmol), P(t-Bu)₃ (0.34 g,1.67 mmol), NaOt-Bu (2.41 g, 25.05 mmol) and toluene (175 mL) wasstirred at 100° C. When the reaction was completed, the reaction productwas extracted with ether and water. And then, the organic layer wasdried with MgSO₄ and concentrated. Then, the concentrate was separatedby silica gel column and recrystallized to obtain 7.06 g (yield: 82%) ofthe product.

Synthesis of 1-1-2

7.08 g (yield: 86%) of the product was obtained by reacting Core 1-1(5.6 g, 17.32 mmol), Sub 1-3 (4.04 g, 17.32 mmol), Pd₂(dba)₃ (0.79 g,0.87 mmol), P(t-Bu)₃ (0.35 g, 1.73 mmol), NaOt-Bu (2.50 g, 25.97 mmol)and toluene (181 mL) by the same method as in synthesis example of1-1-5.

Synthesis of 1-1-26

7.07 g (yield: 82%) of the product was obtained by reacting Core 1-1(3.8 g, 11.75 mmol), Sub 1-34 (5.25 g, 11.75 mmol), Pd₂(dba)₃ (0.54 g,0.59 mmol), P(t-Bu)₃ (0.24 g, 1.18 mmol), NaOt-Bu (1.69 g, 17.63 mmol)and toluene (123 mL) by the same method as in synthesis example of1-1-5.

Synthesis of 1-1-57

7.01 g (yield: 80%) of the product was obtained by reacting Core 1-3(5.3 g, 11.14 mmol), Sub 1-78 (3.87 g, 11.14 mmol), Pd₂(dba)₃ (0.51 g,0.55 mmol), P(t-Bu)₃ (0.23 g, 1.11 mmol), NaOt-Bu (1.61 g, 16.72 mmol)and toluene (117 mL) by the same method as in synthesis example of1-1-5.

Synthesis of 1-1-54

7.11 g (yield: 75%) of the product was obtained by reacting Core 1-5(5.4 g, 12.75 mmol), Sub 1-74 (5.12 g, 12.75 mmol), Pd₂(dba)₃ (0.58 g,0.64 mmol), P(t-Bu)₃ (0.26 g, 1.28 mmol), NaOt-Bu (1.84 g, 19.13 mmol)and toluene (134 mL) by the same method as in synthesis example of1-1-5.

Synthesis of 1-1-61

13.43 g (yield: 75%) of the product was obtained by reacting Core 1-1 (7g, 21.64 mmol), Sub 1-90 (3.7 g, 10.82 mmol), Pd₂(dba)₃ (0.99 g, 1.08mmol), P(t-Bu)₃ (0.44 g, 2.16 mmol), NaOt-Bu (5.20 g, 54.11 mmol) andtoluene (227 mL) by the same method as in synthesis example of 1-1-5.

Synthesis of 2-1-15

7.16 g (yield: 78%) of the product was obtained by reacting Core 1-13(4.1 g, 13.34 mmol), Sub 1-21 (5.56 g, 13.34 mmol), Pd₂(dba)₃ (0.61 g,0.67 mmol), P(t-Bu)₃ (0.27 g, 1.33 mmol), NaOt-Bu (1.92 g, 20.01 mmol)and toluene (140 mL) by the same method as in synthesis example of1-1-5.

Synthesis of 2-2-7

7.05 g (yield: 76%) of the product was obtained by reacting Core 1-18(5.3 g, 17.25 mmol), Sub 1-12 (4.60 g, 17.25 mmol), Pd₂(dba)₃ (0.79 g,0.86 mmol), P(t-Bu)₃ (0.35 g, 1.72 mmol), NaOt-Bu (2.49 g, 25.87 mmol)and toluene (18 mL) by the same method as in synthesis example of 1-1-5.

Synthesis of 3-1-4

7.01 g (yield: 78%) of the product was obtained by reacting Core 1-24 (6g, 18 mmol), Sub 1-11 (4.45 g, 18 mmol), Pd₂(dba)₃ (0.82 g, 0.90 mmol),P(t-Bu)₃ (0.36 g, 1.8 mmol), NaOt-Bu (2.59 g, 26.99 mmol) and toluene(189 mL) by the same method as in synthesis example of 1-1-5.

Synthesis of 3-2-12

7.09 g (yield: 73%) of the product was obtained by reacting Core 1-27(4.6 g, 13.8 mmol), Sub 1-49 (6.23 g, 13.8 mmol), Pd₂(dba)₃ (0.63 g,0.69 mmol), P(t-Bu)₃ (0.28 g, 1.38 mmol), NaOt-Bu (1.99 g, 20.69 mmol)and toluene (145 mL) by the same method as in synthesis example of1-1-5.

V. Synthesis of Final Product(2)

Synthesis of A 1-1-1

The reaction solution mixed with 1-1-1(A) (5.9 g, 12.33 mmol), Sub 2-6(3.64 g, 12.33 mmol), Pd₂(dba)₃ (0.56 g, 0.62 mmol), P(t-Bu)₃ (0.25 g,1.23 mmol), NaOt-Bu (1.78 g, 18.5 mmol) and toluene (129 mL) was stirredat 100° C. When the reaction was completed, the reaction product wasextracted with ether and water. And then, the organic layer was driedwith MgSO₄ and concentrated. Then, the concentrate was separated bysilica gel column and recrystallized to obtain 7.09 g (yield: 83%) ofthe product.

Synthesis of A 1-1-19

7.10 g (yield: 79%) of the product was obtained by reacting 1-1-1(C)(5.8 g, 10.46 mmol), Sub 2-18 (4.03 g, 10.46 mmol), Pd₂(dba)₃ (0.48 g,0.52 mmol), P(t-Bu)₃ (0.21 g, 1.05 mmol), NaOt-Bu (1.51 g, 15.69 mmol)and toluene (110 mL) by the same method as in synthesis example of A1-1-1.

Synthesis of A 1-1-28

7.07 g (yield: 77%) of the product was obtained by reacting 1-1-1(D)(6.2 g, 9.83 mmol), Sub 2-26 (3.78 g, 9.83 mmol), Pd₂(dba)₃ (0.45 g,0.49 mmol), P(t-Bu)₃ (0.20 g, 0.98 mmol), NaOt-Bu (1.42 g, 14.75 mmol)and toluene (103 mL) by the same method as in synthesis example of A1-1-1.

Synthesis of A 1-2-26

7.05 g (yield: 74%) of the product was obtained by reacting 1-2-1(C)(5.9 g, 9.32 mmol), Sub 2-12 (5.13 g, 18.63 mmol), Pd₂(dba)₃ (0.85 g,0.93 mmol), P(t-Bu)₃ (0.38 g, 1.86 mmol), NaOt-Bu (2.69 g, 27.95 mmol)and toluene (98 mL) by the same method as in synthesis example of A1-1-1.

Synthesis of A 2-1-14

7.01 g (yield: 72%) of the product was obtained by reacting 2-1-2(A)(6.4 g, 11.89 mmol), Sub 2-9 (4.3 g, 11.89 mmol), Pd₂(dba)₃ (0.54 g,0.59 mmol), P(t-Bu)₃ (0.24 g, 1.19 mmol), NaOt-Bu (1.71 g, 17.83 mmol)and toluene (125 mL) by the same method as in synthesis example of A1-1-1.

Synthesis of A 3-1-10

7.09 g (yield: 70%) of the product was obtained by reacting 3-1-1(C) (8g, 11.93 mmol), Sub 2-15 (3.09 g, 11.93 mmol), Pd₂(dba)₃ (0.55 g, 0.6mmol), P(t-Bu)₃ (0.24 g, 1.19 mmol), NaOt-Bu (1.72 g, 17.89 mmol) andtoluene (125 mL) by the same method as in synthesis example of A 1-1-1.

The FD-MS values of compounds 1-1-1 to 3-2-10 and A 1-1-1 to A 3-1-10 ofthe present invention manufactured according to the above synthesisexamples are shown in Table 5 below.

TABLE 5 FD-MS of final products compound FD-MS compound FD-MS 1-1-1 m/z= 399.11(C₂₈H₁₇NS = 399.51) 1-1-2 m/z = 475.14(C₃₄H₂₁NS = 475.60) 1-1-5m/z = 515.17(C₃₇H₂₅NS = 515.67) 1-1-7 m/z = 489.12(C₃₄H₁₉NOS = 489.59)1-1-10 m/z = 577.16(C₄₀H₂₃N₃S = 577.70) 1-1-10 m/z = 627.18(C₄₄H₂₅N₃S =627.75) 1-1-23 m/z = 677.19(C₄₈H₂₇N₃S = 677.81) 1-1-26 m/z =733.16(C₅₀H₂₇N₃S₂ = 733.90) 1-1-31 m/z = 633.13(C₄₂H₂₃N₃S₂ = 633.78)1-1-40 m/z = 693.19(C₄₈H₂₇N₃OS = 693.81) 1-1-53 m/z = 743.20(C₅₂H₂₉N₃OS= 743.87) 1-1-56 m/z = 785.20(C₅₄H₃₁N₃S₂ = 785.97) 1-1-57 m/z =900.24(C₆₂H₃₆N₄S₂ = 901.11) 1-1-60 m/z = 826.16(C₅₆H₃₀N₂S₃ = 827.05)1-2-1 m/z = 399.11(C₂₈H₃₇NS = 399.51) 1-2-20 m/z = 677.19(C₄₈H₂₇N₃S =677.81) 1-2-41 m/z = 689.11(C₄₄H₂₃N₃S₃ = 689.87) 2-1-2 m/z =383.13(C₂₈H₁₇NO = 383.44) 2-1-15 m/z = 687.23(C₅₀H₂₉N₃O = 687.78) 2-1-26m/z = 717.19(C₅₀H₂₇N₃OS = 717.83) 2-1-32 m/z = 643.17(C₄₄H₂₅N₃OS =643.75) 2-1-37 m/z = 657.15(C₄₄H₂₃N₃O₂S = 657.74) 2-2-1 m/z =383.13(C₂₈H₃₇NO = 383.44) 2-2-7 m/z = 537.18(C₃₈H₂₃N₃O = 537.61) 2-2-20m/z = 661.22(C₃₈H₂₇N₃O = 661.75) 2-2-29 m/z = 643.17(C₄₄H₂₅N₃OS =643.75) 3-1-1 m/z = 409.18(C₃₁H₂₃N = 409.52) 3-1-4 m/z = 499.19(C₃₇H₂₅NO= 499.60) 3-1-11 m/z = 637.25(C₄₇H₃₁N = 637.77) 3-2-12 m/z =703.26(C₅₁H₃₃N₃O = 703.83) 3-2-16 m/z = 643.21(C₄₅H₂₉N₃S = 643.80) 3-2-1m/z = 409.18(C₃₁H₂₃N = 409.52) 3-2-9 m/z = 637.25(C₄₇H₃₁N₃ = 637.77)3-2-10 m/z = 693.22(C₄₉H₃₁N₃S = 693.86) A 1-1-1 m/z = 692.23(C₅H₃N₂S =692.87) A 1-1-2 m/z = 672.17(C₄₆H₂₈N₂S₂ = 672.86) A 1-1-5 m/z =768.26(C₅₆H₃₈N₂S = 768.96) A 1-1-8 m/z = 782.24(C₅₆H₃₄N₂OS = 782.95) A1-1-9 m/z = 794.28(C₅₈H₃₈N₂S = 795.00) A 1-1-10 m/z = 858.27(C₆₂H₃₈N₂OS= 859.04) A 1-1-15 m/z = 768.26(C₅₆H₃₆N₂S = 768.96) A 1-1-16 m/z =794.28(C₅₈H₃₈N₂S = 795.00) A 1-1-19 m/z = 858.27(C₆₂H₃₈N₂OS = 859.04) A1-1-21 m/z = 809.29(C₅₈H₃₉N₃S = 810.02) A 1-1-28 m/z = 933.32(C₆₈H₄₃N₃S= 934.15) A 1-2-26 m/z = 1021.26(C₇₀H₄₃N₃S₃ = 1022.31) A 2-1-1 m/z =676.25(C₅₀H₃₂N₂O = 676.80) A 2-1-5 m/z = 752.28(C₅₆H₃₆N₂O = 752.90) A2-1-10 m/z = 716.25(C₅₂H₃₂N₂O₂ = 716.82) A 2-1-14 m/z = 818.33(C₆₁H₄₂N₂O= 819.00) A 2-1-15 m/z = 752.28(C₅₆H₃₆N₂O = 752.90) A 2-1-16 m/z =778.30(C₅₈H₃₈N₂O = 778.94) A 2-2-1 m/z = 676.25(C₅₀H₃₂N₂O = 676.80) A2-2-6 m/z = 752.28(C₅₆H₃₆N₂O = 752.90) A 2-2-9 m/z = 778.30(C₅₈H₃₈N₂O =778.94) A 3-1-1 m/z = 702.30(C₅₃H₃₈N₂ = 702.88) A 3-1-5 m/z =778.33(C₅₉H₄₂N₂ = 778.98) A 3-1-6 m/z = 804.35(C₆₁H₄₄N₂ = 805.02) A3-1-10 m/z = 818.33(C₆₃H₄₂N₂O = 819.00)

In the above, even though an exemplary synthesis example of the presentinvention represented by the Formula 1 are described, all of them arebased on Buchwald-Hartwig cross coupling reaction, Pd(II)-catalyzedoxidative cyclization reaction (Org. Lett. 2011, 13, 5504), Miyauraboration reaction and Suzuki cross-coupling reaction. It will beunderstood by those skilled in the art that the above reaction proceedseven when other substituents (substituents of R¹-R¹², L¹, Ar¹ and thelike) defined in Formula 1 are bonded, in addition to the substituentsdescribed in the specific synthesis example.

The above reactions will proceed even if a substituent not specificallymentioned is attached. (A method of synthesizing a core containing Si isdescribed in J. AM. CHEM. SOC. 2008, 130, 7670-7685)

Fabrication and Evaluation of Organic Electronic Element

[Example 1] Red OLED (Phosphorescent Host)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention asluminous host material of a light emitting layer. First, an ITO layer(anode) was formed on a glass substrate, and then a film ofN¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter, “2-TNATA”) was vacuum-deposited on the ITO layer to form ahole injection layer with a thickness of 60 nm. Subsequently, a film ofNPD as a hole transport compound was vacuum-deposited with a thicknessof 60 nm on the hole injection layer to form a hole transport layer. Alight emitting layer with a thickness of 30 nm was formed on the holetransport layer by depositing the compound 1-1-1 of the presentinvention as a host material and (piq)₂Ir(acac) as a dopant material ina weight ratio of 90:10. Next,(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film oftris(8-quinolinolato)aluminum (hereinafter abbreviated as “Alq₃”) wasformed with a thickness of 40 nm to form an electron transport layer.Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then A1 was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

[Example 2] to [Example 25] Red OLED

The OLEDs were fabricated in the same manner as described in Example 1,except that any one of the compounds of the present invention describedin Table 6 below was used as the red host material of a light emittinglayer, instead of the inventive compound 1-1-1.

[Comparative Example 1] to [Comparative Example 4]

The OLEDs were fabricated in the same manner as described in Example 1,except that any one of the following Comparative compounds 1 to 4 wasused as host material of a light emitting layer, instead of theinventive compound 1-1-1.

Electroluminescence (EL) characteristics were measured with aPR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples 1 to 25 of the present invention and ComparativeExamples 1 to 4. And, the T95 life time was measured using a life timemeasuring apparatus manufactured by Macscience Inc. at referencebrightness of 2500 cd/m². The measured results are shown in Table 6below.

TABLE 6 Current Voltage Density Brightness Efficiency Lifetime CIEcompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) X Y comp. Ex(1) comp. Com 16.6 35.2 2500 7.1 63.3 0.65 0.31 comp. Ex(2) comp. Com 2 6.3 27.2 25008.5 79.5 0.66 0.32 comp. Ex(3) comp. Com 3 6.2 29.1 2500 7.7 71.5 0.650.32 comp. Ex(4) comp. Com 4 6.2 32.1 2500 9.1 86.2 0.65 0.31 Ex.(1)Com. 1-1-1 5.4 20.3 2500 12.3 120.1 0.66 0.31 Ex.(2) Com. 1-1-4 5.3 19.52500 12.8 123.7 0.65 0.32 Ex.(3) Com. 1-1-7 5.4 20.2 2500 12.4 132 0.660.32 Ex.(4) Com. 1-1-10 5.4 20.5 2500 12.2 136 0.66 0.31 Ex.(5) Com.1-1-13 5.3 19.8 2500 12.6 139.2 0.66 0.31 Ex.(6) Com. 1-1-23 5.3 18.82500 13.3 142.4 0.65 0.31 Ex.(7) Com. 1-1-31 5.1 14.2 2500 17.6 157.70.66 0.31 Ex.(8) Com. 1-1-41 5.1 15.2 2500 16.5 150.3 0.65 0.31 Ex.(9)Com. 1-1-58 5.3 14.9 2500 16.8 147.2 0.66 0.32 Ex.(10) Com. 1-2-1 5.420.8 2500 12 117.7 0.65 0.31 Ex.(11) Com. 1-2-20 5.4 19.5 2500 12.8138.7 0.66 0.32 Ex.(12) Com. 1-2-41 5.3 16.2 2500 15.4 142.3 0.66 0.32Ex.(13) Com. 2-1-2 5.4 21.2 2500 11.8 115.4 0.66 0.31 Ex.(14) Com.2-1-26 5.4 19.4 2500 12.9 139.6 0.66 0.32 Ex.(15) Com. 2-1-32 5.3 16.42500 15.2 136.2 0.66 0.32 Ex.(16) Com. 2-1-37 5.2 14.8 2500 16.9 149.20.66 0.31 Ex.(17) Com. 2-2-1 5.3 21.0 2500 11.9 113.7 0.66 0.31 Ex.(18)Com. 2-2-20 5.3 20.3 2500 12.3 131.2 0.66 0.31 Ex.(19) Com. 2-2-29 5.216.9 2500 14.8 134.5 0.65 0.31 Ex.(20) Com. 3-1-1 5.5 22.5 2500 10.9109.7 0.66 0.32 Ex.(21) Com. 3-1-11 5.5 21.4 2500 11.7 116.9 0.66 0.31Ex.(22) Com. 3-1-16 5.5 18.9 2500 13.2 125.6 0.66 0.31 Ex.(23) Com.3-2-1 5.5 23.8 2500 9.5 98.7 0.66 0.31 Ex.(24) Com. 3-2-9 5.5 22.5 250010.1 111.5 0.65 0.31 Ex.(25) Com. 3-2-10 5.5 20.5 2500 12.2 120.2 0.660.31

From the results shown in Table 6 above, it is confirmed that theluminous efficiency and lifetime of device are remarkably improved whenthe compound according to an embodiment of the present invention wasused as a phosphorescent host material of a light emitting layer,compared with any one of Comparative compounds 1 to 4

Particularly, comparing six-ring heterocyclic compounds comprising two5-membered rings, while the Comparative compounds 2 and 3 are each N—Ntype having N as a hetero atom in two 5-membered, the compounds of thepresent invention are the type having different hetero atoms such asN—S, N—O, N—CR′R″ or N—SiR′R″. It was confirmed that the the luminousefficiency and lifetime of device are remarkably improved when theinventive compound was used as a phosphorescent host material, comparedto the Comparative compound.

Generally, when molecules are stacked, they have strong electricalinteractions as the number of adjacent it-electrongs increases, which isclosely related to the charge carrier mobility.

In the case of the N—N type six-ring cyclic compound of ComparativeCompound 2 and Comparative Compound 3, when molecules are stacked, theorder of intermolecular arrangement shows the form of edge-to-face dueto heterocyclic core having the homo-type such as N—N type. It isbelieved that this causes low charge carrier mobility and low oxidationstability.

In addition, comparing the comparative compounds 2 and 3, their core hasthe same fused position and two hetero atoms comprised in the core areopposite to each other in direction. It can be seen that the Comparativecompound 2 in which two heteratoms are located in the same directionwith respect to the axis shows the better performance than theComparative compound 3 in which two heteratoms are located in theopposite direction. It is considered that this is because theComparative compound 3 has a relatively non-linear structure compared tothe Comparative compound 2 and thus the charge transfer from the host tothe dopant is not smooth as the difference of the T1 value between thehost and the dopant increases.

The six-ring cyclic compound of the present invention has a heterocycliccore in which heteroatoms are different from each other. Therefore, thecompound of the present invention has the antiparallel cofacialit-stacking structure as the molecular packing structure. This allowsthe molecules to be arranged as form of the face-to-face. It is believedthat the steric effect of Ar1 bonded to heteroatom N, wherein theheteroatom arranged asymmetrically is the cause of the packingstructure, causes significantly higher carrier mobility and thus theefficiency of device is increased and the life time of device issignificantly increased due to high oxidation stability.

In addition, comparing Comparative compound 4 with the compound of thepresent invention, T1 and the energy band gap are dependent on the fusedposition of the six-ring cyclic compound, that is, the degree of twistof the molecular, wherein Comparative compound 4 and the inventivecompound are similar in having N—S type in the six-ring cyclic compound,but have difference in the fused position of carbazole core.

The core of the inventive compound has a structure that is less bentthan the Comparative compound 4, and thus the T1 value of the inventivecompound is relatively lower. Therefore, it is seen that the efficiencyis increased because the charge transfer from the host to the dopant issmooth and the number of surplus polarons is decreased.

Particularly, the compound having a specific substituent such asbenzothienopyrimidine or benzofuropyrimidine of the inventive compoundsexhibits the best device results, compared to the compound havinggeneral aryl groups or general heterocyclic groups as a substituent. Itis believed that this is because the inventive compound has a structuresuitable for accommodating both holes and electrons by introducing twonitrogen atoms (N) into the core (dibenzothiophene, dibenzofuran) havingstrong hole characteristics, resulting in the easier charge balance ofholes and electrons and thus the light emission in the light emittinglayer is performed efficiently.

From the result of table 6 above, it is suggested that the efficiencyand the lifetime may be dependent on the the type of heteroatom includedin six-ring cyclic compound. That is, it is seen that the band gap, theelectrical characteristics, the interface characteristics and the likecan be largely changed depending on the kind and the bonding position ofsubstituent. Particularly, in the case of phosphorescent host, becausethe correlation of the hole transfer layer and the dopant is grasped,even if a similar core is used, it will be very difficult to deduce theexcellent electrical characteristics of the inventive compound showingin the phosphorescent host.

[Example 26] Green OLED (a Hole Transport Layer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as ahole transport layer material. First, an ITO layer (anode) was formed ona glass substrate, and then 2-TNATA was vacuum-deposited on the ITOlayer to form a hole injection layer with a thickness of 60 nm.Subsequently, the compound A 1-1-1 of the present invention wasvacuum-deposited with a thickness of 60 nm on the hole injection layerto form a hole transport layer. Subsequently, a light emitting layerwith a thickness of 30 nm was formed on the hole transport layer bydepositing 4,4′-N,N′-dicarbazole-biphenyl (hereinafter, “CBP”) as a hostmaterial and tris(2-phenylpyridine)-iridium (hereinafter, “Ir(ppy)₃)”)as a dopant material in a weight ratio of 90:10. Next, BAlq wasvacuum-deposited with a thickness of 10 nm on the light emitting layerto form a hole blocking layer, and Alq₃ was vacuum-deposited with athickness of 40 nm on the hole blocking layer to form an electrontransport layer. Next, LiF as halogenated alkali metal was depositedwith a thickness of 0.2 nm on the electron transport layer to form anelectron injection layer, and then A1 was deposited with a thickness of150 nm on the electron injection layer to form a cathode. In this way,the OLED was completed.

[Example 27] to [Example 49] Green OLED (a Hole Transport Layer)

The OLEDs were fabricated in the same manner as described in Example 26,except that any one of the compounds 1-1-2 to A 3-1-6 of the presentinvention described in Table 7 below was used as the hole transportlayer material, instead of the inventive compound A 1-1-1.

[Comparative Example 5] to [Comparative Example 7]

Comparative example 5 was fabricated in the same manner as described inexample 26 above, except that comparative compound 5 was used as thehole transport layer material, instead of the inventive compound A1-1-1.

Comparative example 6 was fabricated in the same manner as described inexample 26 above, except that comparative compound 6 instead of thecompound A 1-1-1 of the present invention was used as the hole transportlayer material.

Comparative example 7 was fabricated in the same manner as described inexample 26 above, except that comparative compound 7 instead of thecompound A 1-1-1 of the present invention was used as the hole transportlayer material.

Electroluminescence (EL) characteristics were measured with aPR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples 26 to 49 of the present invention and ComparativeExamples 5 to 7. And, the T95 life time was measured using a life timemeasuring apparatus manufactured by Macscience Inc. at referencebrightness of 5000 cd/m². The measured results are shown in Table 7below.

TABLE 7 Current Voltage Density Brightness Efficiency Lifetime CIEcompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comp. Ex(5) comp. Com 55.8 21.7 5000 23 59.6 0.33 0.62 comp. Ex(6) comp. Com 6 5.7 18.7 500025.7 77 0.33 0.61 comp. Ex(7) comp. Com 7 5.5 17.7 5000 28.2 89.9 0.320.62 Ex.(26) Com. A 1-1-1 5.2 12.3 5000 40.6 141.2 0.33 0.61 Ex.(27)Com. A 1-1-2 5.3 11.5 5000 43.5 145.1 0.33 0.61 Ex.(28) Com. A 1-1-5 5.210.7 5000 46.7 149.3 0.33 0.61 Ex.(29) Com. A 1-1-8 5.2 10.3 5000 48.5153.4 0.33 0.62 Ex.(30) Com. A 1-1-9 5.1 9.5 5000 52.6 158.2 0.33 0.62Ex.(31) Com. A 1-1-10 5.1 9.4 5000 53.3 164.4 0.32 0.62 Ex.(32) Com. A1-1-11 5.1 9.5 5000 52.8 161.5 0.32 0.62 Ex.(33) Com. A 1-1-15 5.2 9.75000 51.3 156.6 0.33 0.62 Ex.(34) Com. A 1-1-16 5.1 9.5 5000 52.8 159.20.32 0.62 Ex.(35) Com. A 1-1-21 5.2 11.0 5000 45.5 152.8 0.32 0.62Ex.(36) Com. A 1-2-1 5.3 12.7 5000 39.5 136.2 0.32 0.61 Ex.(37) Com. A1-2-6 5.3 11.9 5000 42.1 139.7 0.32 0.61 Ex.(38) Com. A 1-2-9 5.3 11.35000 44.3 142.8 0.33 0.61 Ex.(39) Com. A 2-1-1 5.3 14.0 5000 35.6 130.20.33 0.62 Ex.(40) Com. A 2-1-5 5.3 13.2 5000 37.8 133.5 0.32 0.62Ex.(41) Com. A 2-1-10 5.3 12.5 5000 40.1 137.3 0.32 0.61 Ex.(42) Com. A2-1-15 5.3 14.0 5000 35.8 132.2 0.32 0.61 Ex.(43) Com. A 2-1-16 5.3 13.45000 37.4 138.6 0.32 0.61 Ex.(44) Com. A 2-2-1 5.3 15.1 5000 33.2 125.20.33 0.62 Ex.(45) Com. A 2-2-6 5.3 14.2 5000 35.1 127.8 0.33 0.62Ex.(46) Com. A 2-2-9 5.3 13.3 5000 37.6 130.4 0.32 0.62 Ex.(47) Com. A3-1-1 5.4 16.3 5000 30.7 120.1 0.32 0.62 Ex.(48) Com. A 3-1-5 5.4 15.95000 31.5 122.9 0.33 0.62 Ex.(49) Com. A 3-1-6 5.4 15.3 5000 34.7 1280.33 0.61

From the results shown in Table 7, it is confirmed that the luminousefficiency and lifetime of the organic electroluminescent device areremarkably improved when compounds of the present invention were used asa hole transport layer material, compared with Comparative compounds 5to 7.

The inventive compound capable of using as hole transport layer materialby introducing —N(R^(a)) (R^(b)) into a 6-ring heterocyclic core of theinventive compound has a high HOMO energy level, wherein HOMO energylevel is the intrinsic properties of the material. This causes thecharge balance to increases and the surplus polaron to decrease in thelight emitting layer, and thus the interface deterioration and dopantquenching due to the surplus polar are reduced.

In the case of the N—N type six-ring cyclic compound of ComparativeCompound 6, when molecules are stacked, the order of the intermoleculararrangement becomes the form of the edge-to-face since the heterocycliccore is the homo type of N—N type. It is considered that this causes lowcharge carrier mobility and low oxidation stability.

The packing structure of the molecule of the inventive compoundcomprising a six-ring cyclic compound is an antiparallel cofacialπ-stacking structure since the inventive compound has the heterocycliccore in which heteroatoms are different from each other. This allows themolecules to be arranged as form of the face-to-face. It is believedthat the steric effect of Ar1 bonded to heteroatom N, wherein theheteroatom arranged asymmetrically is the cause of the packingstructure, causes significantly higher carrier mobility and thus theefficiency of device is increased and the life time of device issignificantly increased due to high oxidation stability.

In addition, among the compounds of the present invention, the compoundof non-linear type exhibited more performance than that of linear type,wherein non-linear type means that the core and the amine group arebonded to the linker (L¹, L′) at the ortho- or meta-position and lineartype means that the core and the amine group are bonded to the linker(L¹, L′) at the para position. It is considered that this is because thebonding angle becomes smaller and thus T1 value becomes higher,resulting in improving the ability capable of blocking electron.

It is confirmed that the lifetime is remarkably improved as well as thelow driving voltage and high luminous efficiency even when the compoundof the present invention was used as a hole transporting layer material.

From the results shown in Table 7, it is difficult to infer theefficiency and lifetime due to the difference in the fused position andtype and arrangement of heteroatom in the six-ring cyclic compound.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

1. A compound of Formula 1 below:

wherein, X and Y are each independently O, S, C(R¹³)(R¹⁴) orSi(R¹³)(R¹⁴), wherein R¹³ and R¹⁴ are each independently selected fromthe group consisting of hydrogen, deuterium, a C₁-C₅₀ alkyl group, aC₂-C₃₀ alkenyl group, a C₂-C₃₀ alkynyl group, a C₁-C₃₀ alkoxyl group, aC₆-C₃₀ aryloxyl group, a C₁-C₃₀ silyl group, a C₆-C₆₀ aryl group, aC₂-C₆₀ heterocyclic group comprising at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a fluorenyl group, afused ring group of a C₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring,and -L′-N(R^(a))(R^(b)), and R¹³ and R⁴ is optionally linked to eachother to form a spiro-compound together with C or Si to which R¹³ andR¹⁴ are bond, m and n are each an integer of 0 or 1, and m+n is aninteger of 1 or more, R¹ to R¹² are each independently selected from thegroup consisting of hydrogen, deuterium, a halogen, a C₆-C₆₀ aryl group,a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring,a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₁-C₅₀ alkynyl group, aC₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxyl group, and -L′-N(R^(a))(R^(b)),and neighboring groups of R¹ to R¹² are optionally linked to each otherto form a ring, L¹ is selected from the group consisting of a singlebond; a C₆-C₆₀ arylene group; a fluorenylene group; a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring formed by a C₆-C₆₀aromatic ring and a C₃-C₆₀ aliphatic ring, Ar¹ is selected from thegroup consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, and -L′-N(R^(a))(R^(b)), in-L′-N(R^(a))(R^(b)) above, L′ is selected from the group consisting of asingle bond; a C₆-C₆₀ arylene group; a fluorenylene group; a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; and a fused ring of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, and L′ may be furthersubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group, a siloxane group, aboron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkyl group, aC₇-C₂₀ arylalkyl group, a C₈-C₂₀ arylalkenyl group and —N(R^(a))(R^(b)),in -L′-N(R^(a))(R^(b)) and —N(R^(a))(R^(b)) above, R^(a) and R^(b) areeach independently selected from the group consisting of a C₆-C₆₀ arylgroup; a fluorenyl group; a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P; and a fused ring of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring, and when R¹-R¹⁴, L¹, Ar¹, R^(a) and R^(b) are each an aryl group,a fluorenyl group, a heterocyclic group, a fused ring group, an alkylgroup, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxygroup, an arylene group or a fluorenylene group, they may be eachfurther substituted with one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aC₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, aC₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkylgroup, a C₇-C₂₀ arylalkyl group and a C₈-C₂₀ arylalkenyl group.
 2. Thecompound of claim 1, wherein Formula 1 above is represented by one ofthe following Formulas 2 to 5:

in formulas 2 to 5, R¹ to R¹², L¹, X, Y, and Ar¹ are the same as definedin claim 1, Z ring is a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P, and X¹ to X⁴ are each independently N,C or C(R¹³), any one of X¹ to X⁴ is C and at least one of the others isN, wherein R¹³ is the same as defined in Formula
 1. 3. The compound ofclaim 2, wherein Z ring above is represented by one of the followingFormulas Z′-1 to Z′-9:

in formulas Z′-1 to Z′-9, “*” indicates the position fused with ringcontaining X¹ to X⁴, V is independently C(R¹³) or N, and W¹ and W² areeach independently a single bond, C(R¹³)(R¹⁴), N(Ar²), O, S, orSi(R¹³)(R¹⁴), wherein Ar² is the same as Ar¹ defined in claim 1 and R¹³and R¹⁴ are the same as defined in claim
 1. 4. The compound of claim 2,the form fused of the ring consisting X¹-X⁴ and the Z ring is one of thefollowing Formulas Z-10 to Z-25:

in Formulas Z-1 to Z-22 above, Ar³ is the same as Ar¹ defined in claim1, and W¹ and W² are each independently a single bond, C(R¹³)(R¹⁴),N(Ar²), O, S or Si(R¹³)(R¹⁴), wherein Ar² is the same as Ar¹ defined inclaim 1 and R¹³ and R¹⁴ are the same as defined in claim
 1. 5. Thecompound of claim 1, wherein Formula 1 above is represented by thefollowing formula:

in Formula 6 above, Ar¹, L¹, L′ X, Y, m, n, R^(a) and R^(b) are the sameas defined in claim 1, R²³ to R²⁵ are the same as R¹ to R¹² defined inclaim 1, a1 and a2 are each an integer of 0 or 1 and a1+a2=1, and p1 andp2 are each an integer of 0-4.
 6. The compound of claim 1, wherein L′ isselected from the group of the following Formulas:

in the Formulas above, R²¹ to R²³ are each independently selected fromthe group consisting of hydrogen, deuterium, halogen, a silane group, asiloxane group, a boron group, a germanium group, a cyano group, a nitrogroup, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ arylgroup, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenylgroup, a C₂-C₂₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P, a C₃-C₂₀cycloalkyl group, a C₇-C₂₀ arylalkyl group, a C₈-C₂₀ arylalkenyl group,and —N(R^(a))(R^(b)), wherein R^(a) and R^(b) are the same as defined inclaim 1, b1 is an integer of 0 to 4, b2 is an integer of 0 to 6, b3 isan integer of 0 to 5, b4 is an integer of 0 to 8, and when b1 to b4 areeach an integer of 2 or more, neighboring R²¹ to neighboring R²³ areoptionally linked to each other to form a ring, and A is N(Ar²), O, S,C(R¹³)(R¹⁴) or Si(R¹³)(R¹⁴), wherein Ar² is the same as Ar¹ defined inclaim 1 and R¹³ and R¹⁴ are the same as defined in claim
 1. 7. Thecompound of claim 1, wherein the compound represented by Formula 1 aboveis one of the following compounds:


8. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound of claim
 1. 9. The organic electric element ofclaim 8, wherein the compound is comprised in at least one layer of ahole injection layer, a hole transport layer, an emission-auxiliarylayer and a light emitting layer, and the compound is comprised as asingle compound or as a component of the mixture of two or more kinds.10. The organic electric element of claim 9, wherein the compound isused as phosphorescent host material of the light emitting layer. 11.The organic electric element of claim 9, wherein the compound is used asred phosphorescent host material of the light emitting layer.
 12. Theorganic electric element of claim 8, further comprising a layer forimproving luminous efficiency formed on one side of the first electrodeand/or one side of the second electrode, the side facing the organicmaterial layer.
 13. The organic electric element of claim 8, wherein theorganic material layer is formed by one of the processes of spincoating, nozzle printing, inkjet printing, slot coating, dip coating androll-to-roll.
 14. An electronic device comprising a display device and acontrol unit for driving the display device, wherein the display devicecomprises the organic electric element of claim
 8. 15. The electronicdevice of claim 14, wherein the organic electric element is an organiclight emitting diode, an organic solar cell, an organic photo conductor,an organic transistor, or an element for monochromatic or whiteillumination.